title: Halonium ion triggered rearrangement of unsaturated benzo-annulated bi- and tricyclic sulfonamides.
abstract: The halonium ion mediated 1,2-Wagner-Meerwein-type rearrangement of a series of benzo-fused bi- and tricyclic sulfonamides is reported. During this rearrangement the carbon-carbon bond that migrates was selectively set in the intramolecular Mizoroki-Heck (IHR) synthesis of the starting materials. Consequently, this method constitutes a means to access the regioisomeric series of cyclic sulfonamides not observed during the Mizoroki-Heck reaction.
authors.affiliation: Centre for Synthesis and Chemical Biology, School of Chemistry and Chemical Biology, University College Dublin , Dublin 4, Ireland.
authors.forename: Kimberly
authors.initials: K
authors.lastname: Geoghegan
authors.forename: Shaun
authors.initials: S
authors.lastname: Smullen
authors.forename: Paul
authors.initials: P
authors.lastname: Evans
mesh_terms: D052117:Benzodioxoles / Q000737:chemistry*; D002384:Catalysis; D006846:Hydrocarbons, Halogenated / Q000737:chemistry*; D007477:Ions / Q000737:chemistry*; D015394:Molecular Structure; D011084:Polycyclic Aromatic Hydrocarbons / Q000737:chemistry*; D013237:Stereoisomerism; D013449:Sulfonamides / Q000737:chemistry*
chemical_list: C000588957:1-bromo-3,4-(methylenedioxy)benzene; D052117:Benzodioxoles; D006846:Hydrocarbons, Halogenated; D007477:Ions; D011084:Polycyclic Aromatic Hydrocarbons; D013449:Sulfonamides